Do People Still Invite Their Bosses Over for Dinner?

If period movies and television shows are telling us the truth, and we all know they never lie, then it was common practice around the middle of last century for underlings to invite their bosses over for dinner. Just two couples, enjoying a perfectly awkward meal in uncomfortable silence. Thank goodness everyone drank voluminously back then or there would have been no way to get through the evening.

The question posed here is, do people still do this, or has the practice died away along with smoking in the office and three martini lunches?

Overall, the internet is split. Many people fall squarely on the side of antiquated business practice. In an interview with BravoTV workplace expert Alison Green expressed the opinion that it’s generally a bad idea. She said, “It’s blurring the boundaries in a way that isn’t great—ultimately, this is a work relationship, not a social one. Your boss needs to be able to, for example, give you tough feedback and it’s going to feel a lot weirder to do that if he was a guest in your home a week ago.”

But others are more optimistic. However, even those that seem to support the practice do so with a number of caveats along for the ride.

The Invitation

The invitation, which should be the easy part, is already loaded with potential hazards. You want to be certain your boss doesn’t interpret your invitation as an attempt to brown nose. Which is interesting because back when dinner with the boss was common, that’s exactly what it was, an attempt to curry favor. You knew it. Your boss knew it. And everyone just played along.

Today though this sort of overt gesture is frowned upon and viewed as desperate. The best way to avoid this is to invite your boss to dinner only if you have a good, friendly relationship with them already. Then your invitation is seen for what it is, a chance for work friends to get to know each other better. If your corporate culture is buttoned up and stuffy, or your relationship with your boss fairly formal, broaching dinner may not be a good idea.

The Meal

According to The Muse, a dinner at home with the boss is already fraught with risk. No need to further complicate things. Keep it simple. Don’t slave in the kitchen preparing a five course meal. That’s a disaster waiting to happen, and it looks desperate. Instead prepare something that most people like and that you’re familiar with. We’ve already learned that boss dinners aren’t about impressing them like they were 70 years ago. So add nice touches, certainly, but keep things grounded.

Casual seems to be the advice most often given. Treat your boss to an backyard BBQ or a light cocktail hour followed by a simple but delicious meal.  It’s also common to invite other coworkers to help lighten the evening and lift the anvil of awkwardness that might otherwise press down on the event.

Remember that your boss is a person that enjoys a good time just like you do, so try not to be nervous. If you enjoy yourself you’ll help put everyone at ease, and an evening that might otherwise make you want to vault off the balcony could turn into a nice, memorable night.

And you might end up scoring points with the boss, even though that certainly was never your plan all along.


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